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Merck
CN

D90008

Diethyl azodicarboxylate

Synonym(s):

DEAD

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About This Item

Linear Formula:
C2H5OCON=NCOOC2H5
CAS Number:
1972-28-7
Molecular Weight:
174.15
EC Number:
217-821-7
UNSPSC Code:
12352108
PubChem Substance ID:
329798884
Beilstein/REAXYS Number:
908662
MDL number:
MFCD00009103

Key Documents

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InChI key

FAMRKDQNMBBFBR-BQYQJAHWSA-N

InChI

1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+

SMILES string

CCOC(=O)\N=N\C(=O)OCC

form

liquid

impurities

<3% dichloromethane

refractive index

n20/D 1.43 (lit.)

bp

106 °C/13 mmHg (lit.)

density

1.106 g/mL at 25 °C (lit.)

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Application

Reagent used in Mitsunobu and Diels-Alder reactions, as well as in allylic amination of alkenes.

pictograms

Exploding BombExclamation mark
GHS01,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Expl. 1.1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

1 - Explosive hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
04823BW
15914EF
10614JS
10114KZ
09615PY

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F K Brown et al.
Journal of medicinal chemistry, 37(5), 674-688 (1994-03-04)
Systematic modification of the presumed P1 side chain in a series of (carboxyalkyl)amino-based inhibitors of matrix metalloproteinases enabled identification of the 2-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)ethyl group as a preferred substituent imparting potent inhibition of the enzymes collagenase and gelatinase. It was subsequently found
The Journal of Organic Chemistry, 58, 5261-5261 (1993)
The Journal of Organic Chemistry, 58, 4979-4979 (1993)
Jetze Visser et al.
Nature communications, 6, 6933-6933 (2015-04-29)
Despite intensive research, hydrogels currently available for tissue repair in the musculoskeletal system are unable to meet the mechanical, as well as the biological, requirements for successful outcomes. Here we reinforce soft hydrogels with highly organized, high-porosity microfibre networks that
Adrian Egli et al.
The Journal of infectious diseases, 210(5), 717-727 (2014-03-13)
Feedback mechanisms between interferons α and λ (IFNs) may be affected by single nucleotide polymorphisms (SNP) in interleukin 28B (IL-28B; IFN-λ3) promoter region and may influence cytomegalovirus (CMV) replication. We associated IL-28B SNPs with the risk of CMV replication after
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